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Encyclopedia Britannica



COCAINE, C17H21NO4

This article appears in Volume V06, Page 615 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: CLI-COM
COCAINE, C17H21NO4 , an alkaloid occurring to the extent of about 1% in the leaves of Erythroxylon
coca
  (see above).
It is associated with many other alkaloids: cinnamyl
cocaine, C19H23NO4; a-truxilline (C19H23N04)2; /3-truxilline,
(C19H23N04)2; benzoylecgonine, C,6H,9NO2; tropa-cocaine,
C13H19NO2; hygrine, C8H15NO; cuscohygrine, C,3H24NO2.
These substances, which may be collectively termed " cocaines," are all derivatives of
ecgonine
  (q.v.). Cocaine is benzoylmethyl
ecgonine
 . It crystallizes from
alcohol
  in prisms, which are sparingly soluble in water. Its solution has a
bitter
 
taste
 , alkaline reaction, and is laevorotatory. Its use as a local anaesthetic (see
ANAESTHESIA
 ) makes it the most valuable of the
coca
  alkaloids, and it is much used in ophthalmic practice. Applied to the conjunctiva it causes
anaesthesia
 , dilatation of the pupil, diminution of the intraocular tension, and some interference with
accommodation
 . The conversion of the mixture obtained by extracting coca-leaves into cocaine is effected by saponifying the esters into ecgonine and the respective acids, and then benzoylating and methylating the ecgonine. Homologues of cocaineethylbenzoylecgonine, &c. have been prepared; they closely resemble natural cocaine. Cinnamyl cocaine is cinnamylmethylecgonine, i.e. cocaine in which the benzoyl group is replaced by the cinnamyl group. a- and fl-truxillines, named from their
isolation
  from a coca of Truxillo .(Peru), are two isomeric alkaloids which hydrolyse to ecgonine, methyl
alcohol
 , and two isomeric acids, the truxillic acids, C18H1604. T'he alkaloids are therefore methyl truxillylecgonines. The truxillic acids have been studied by K. Liebermann and his students (Ber., vols. 21-27, and 31), and are
diphenyl
  tetra-methylene dicarboxylic acids.


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